title: Isolation and identification of a sibutramine analogue adulterated in slimming dietary supplements.
abstract: A suspected sibutramine analogue was detected in a slimming functional food by an ultra performance liquid chromatography-electrospray ionisation-time of flight mass spectrometry (UPLC-ESI-TOF/MS) method. The ultraviolet (UV) spectrum of this suspected compound showed close similarity to that of sibutramine. The sample was extracted with 70% MeOH and isolated by semi-preparative column chromatography. The structure of this compound was identified by spectroscopic analyses (nuclear magnetic resonance [NMR] technique, mass and tandem mass etc.). The structure of the unknown compound was demonstrated to be [(±)-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine (molecular formula C17H25NCl2) and named as chloro-sibutramine. Compared with sibutramine, it has one more chlorine atom than the 3-cholorophenyl group so was switched to 3,4-dichlorophenyl. Until now, chloro-sibutramine was isolated for the first time from the undeclared ingredient included in dietary supplements. Although the safety of chloro-sibutramine is unknown, there is a potential health risk to consumers because of a similar skeleton to sibutramine. For public health, this sibutramine analogue has been included in the inspection list of illegal adulterants in Korea.
authors.affiliation: Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration complex, 187 Osongsaengmyeong2-ro, Cheongwon-gun 363-700, Chungcheongbuk-do, Korea.
authors.forename: Ji Won
authors.initials: JW
authors.lastname: Kim
authors.forename: Soon Jae
authors.initials: SJ
authors.lastname: Kweon
authors.forename: Seon Kyung
authors.initials: SK
authors.lastname: Park
authors.forename: Jung Yeon
authors.initials: JY
authors.lastname: Kim
authors.forename: Ji Hyun
authors.initials: JH
authors.lastname: Lee
authors.forename: Kyoung Moon
authors.initials: KM
authors.lastname: Han
authors.forename: Sooyeul
authors.initials: S
authors.lastname: Cho
authors.forename: Jinho
authors.initials: J
authors.lastname: Kim
authors.forename: Soon Young
authors.initials: SY
authors.lastname: Han
authors.forename: Hyoung Ja
authors.initials: HJ
authors.lastname: Kim
authors.forename: Woo Seong
authors.initials: WS
authors.lastname: Kim
mesh_terms: D001067:Appetite Depressants / Q000032:analysis*; D002853:Chromatography, Liquid; D003503:Cyclobutanes / Q000032:analysis* / Q000737:chemistry; D019587:Dietary Supplements; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy
chemical_list: D001067:Appetite Depressants; D003503:Cyclobutanes; C058254:sibutramine